Legacy Systems and Disconnected Data

Kapil Gupta, former Enterprise AI Product & Platform Leader at Cigna, shares insights from more than two decades of turning cutting-edge technology into enterprise-ready products. He unpacks the difference between generative AI and agentic AI, and why governance, user choice, and thoughtful design matter just as much as innovation.

Learn how enterprises can scale responsibly and why the best technology often feels invisible to the people using it.

Key Takeaways:

• The tangible difference between generative AI and agent-based workflows

• Why adoption depends on fitting into existing workflows, rather than forcing behavior change

• The challenge of legacy systems and disconnected data

• How companies can innovate quickly without introducing unnecessary risk

• How pushing back, probing, and questioning AI can unlock more value

• Why listening to users matters more than building flashy features

Guest Bio: Kapil Gupta is an executive product leader specializing in leveraging emerging technologies to solve complex business problems at scale. As a leader of AI product and platform teams at Cigna and previously at industry leaders like Capital One, Deloitte, and IBM, he has turned breakthrough innovations like Generative AI into practical enterprise solutions.

Kapil is driven by a focus on crafting AI-driven product experiences that solve real problems and ensure high adoption, bridging the gap between sophisticated technology and business value. He balances high-level strategic vision with a passion for staying hands-on, often vibe coding prototypes to prove out new concepts. Kapil holds an MS in Computer Science and an MBA from NYU Stern. He shares his work at kapilgupta.me and lives in New York.

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About this Show:

The Brave Technologist is here to shed light on the opportunities and challenges of emerging tech. To make it digestible, less scary, and more approachable for all!

Join us as we embark on a mission to demystify artificial intelligence, challenge the status quo, and empower everyday people to embrace the digital revolution. Whether you're a tech enthusiast, a curious mind, or an industry professional, this podcast invites you to join the conversation and explore the future of AI together.

The Brave Technologist Podcast is hosted by Luke Mulks, VP Business Operations at Brave Software—makers of the privacy-respecting Brave browser and Search engine, and now powering AI everywhere with the Brave Search API.

Music by: Ari Dvorin

Produced by: Sam Laliberte